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Enantioselective synthesis of gamma-tetrasubstituted nitrosulfonyl carboxylates and amides via L-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides

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Title Enantioselective synthesis of gamma-tetrasubstituted nitrosulfonyl carboxylates and amides via L-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides
 
Creator BERA, K
NAMBOOTHIRI, INN
 
Subject MATRIX-METALLOPROTEINASE INHIBITORS
ALPHA-KETO ESTERS
MICHAEL-ADDITION
VINYL SULFONES
ALPHA,BETA-UNSATURATED ALDEHYDES
ORGANOCATALYTIC ADDITION
ASYMMETRIC CATALYSIS
CHIRAL SQUARAMIDES
1,3-DIPOLAR CYCLOADDITION
AMINO-ACIDS
 
Description Michael addition of alpha-nitrosulfones to aryl-and alkyl acrylates and acrylamides proceeds in the presence of 5-10 mol% of an amino acid derived new organocatalyst to provide gamma-tetrasubstituted gamma-nitro-gamma-sulfonyl carboxylates and amides in excellent yields and enantioselectivities. Scale-up of the reaction to multi-grams, convenient recovery of the catalyst and its recyclability without any drop in yield and selectivity are attractive features of this methodology.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-28T12:11:39Z
2014-12-28T12:11:39Z
2014
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 12(33)6425-6431
1477-0520
1477-0539
http://dx.doi.org/10.1039/c4ob00344f
http://dspace.library.iitb.ac.in/jspui/handle/100/16458
 
Language English